7 best tools for live chat upselling in 2025

I remember stumbling across a Reddit thread from a tech support agent who was suddenly told their team had to start making sales. They were, understandably, freaking out. These were people who got into support because they liked fixing problems, not because they wanted to badger customers into buying more stuff. The new pressure turned a job they once enjoyed into a daily grind of awkward pitches and irritated users.

Does that hit a little too close to home? It’s a tightrope walk so many businesses are on. You need to grow, but the last thing you want to do is turn your helpful support team into a pushy sales engine. That’s a fast way to burn through the trust you’ve worked so hard to build.

Luckily, you don’t have to choose between the two. Modern tools, especially those with a bit of AI smarts, have really changed things. Good live chat upselling isn't about jamming a sales pitch into a support ticket. It's about spotting an opportunity to add more value and solve a customer's next problem, sometimes before they even know they have one. It’s about making a conversation genuinely more helpful.

In this article, I’ll walk you through the top 7 tools I've found that help you bump up your average order value (AOV) through conversations that are timely, useful, and actually appreciated.

What is live chat upselling?

At its heart, live chat upselling is just suggesting a better product, a helpful add-on, or a related service during a real-time chat. But let's be really clear about something: this is not about the hard sell.

Upselling that actually works is all about the customer. It comes from listening to what someone needs and having that "aha" moment where you realize, "You know, they'd have a much better time with this other option." It’s a little different from cross-selling, which is more about suggesting related but separate items (like offering floor mats after someone buys a new car). Upselling is about upgrading the original purchase itself (like suggesting the model of the car with the sunroof and better sound system).

The real goal here is for everyone to win. The customer leaves with a solution that’s a perfect fit for them, maybe in a way they hadn't even thought of. And your business grows, not just from one bigger sale, but by building the kind of loyalty that keeps people coming back.

How we chose the best tools for live chat upselling

To cut through all the marketing noise, I focused on what really counts when you're trying to be helpful without being annoying. Here’s the checklist I used to put this list together:

1. AI and Automation Smarts: How clever is the tool, really? I looked for platforms that use AI to figure out what a customer is trying to do and then make relevant, personal suggestions that feel like good advice, not a canned script.

2. Plays Well with Others: A new tool shouldn't force you to tear down your entire setup. I gave priority to tools that plug right into the helpdesks you’re probably already using, like Zendesk or Freshdesk, without a massive migration project.

3. Easy to Get Started: Can you actually get it up and running without needing a team of developers or sitting through a month of sales calls? Big points went to tools that are self-serve and let you see results in minutes.

4. Customization and Control: You know your brand's voice better than anyone. The best tools let you control the AI's personality, decide what triggers a proactive message, and choose the exact knowledge it should use.

5. Transparent Pricing: Nobody likes getting a surprise bill. I hunted for clear, predictable pricing that doesn't penalize you for having a busy month with confusing fees for every ticket it touches.

Comparison of the best live chat upselling tools

Here’s a quick side-by-side look at how the top tools compare.

Tool	Best For	Standout Feature	Pricing Model
eesel AI	Adding AI to any helpdesk seamlessly	Risk-free simulation on past tickets	Flat-rate, based on interactions
Gorgias	Shopify & e-commerce stores	Deep e-commerce platform integration	Per-ticket & tiered plans
Intercom	All-in-one proactive messaging	"Fin" AI Agent & Messenger suite	Per-seat & per-resolution fees
LiveChat	Sales-focused teams	Product Cards & sales tracking	Per-seat, tiered plans
Tidio	Small e-commerce businesses	"Lyro" AI with a free starting plan	Free & per-seat plans with AI limits
Zendesk	Enterprise teams needing a full suite	Integrated helpdesk & AI ecosystem	Per-seat, tiered plans
Freshdesk	Businesses using the Freshworks suite	Unified agent workspace & Freddy AI	Per-seat, tiered plans

The 7 best tools for live chat upselling in 2025

1. eesel AI

eesel AI is built for teams who want to add smart, value-first AI into their support channels without having to abandon the helpdesk they already know and love. It’s not another giant platform that makes you move everything over. Instead, it’s a clever layer that connects in minutes with tools you already use, including Zendesk, Freshdesk, and Gorgias.

What makes eesel AI great for upselling is its ability to learn directly from your past support conversations. This means its suggestions are grounded in your team's real-world interactions and match your unique brand voice. It already knows what works for you. The best part, though, is its simulation mode. You can test the AI on thousands of your past tickets before it ever goes live with a customer. This lets you launch with total confidence, knowing it will only jump in when and where you want it to.

A screenshot of the eesel AI simulation mode, demonstrating how to test the effectiveness of live chat upselling strategies on past tickets.

Pros & Cons

• Pros: Super easy self-serve setup (you can be live in minutes), no need to "rip and replace" your helpdesk, fully customizable AI actions and personality, clear pricing without surprise per-resolution fees.

• Cons: It's a newer tool compared to some of the old guard, and setting up advanced custom API actions might take a little configuration.

Pricing

eesel AI has straightforward pricing based on how much you use it, not on resolutions or how many agents you have.

• Team: $299/month ($239/month if billed annually) for up to 1,000 interactions.

• Business: $799/month ($639/month if billed annually) for up to 3,000 interactions, plus features like training on past tickets and AI Actions.

• Custom: Custom plans are available for unlimited interactions and more advanced needs.

2. Gorgias

Gorgias is a beast for e-commerce brands, particularly if you're on Shopify. Its biggest win is how deeply it connects with e-commerce platforms. Agents can see order details, process refunds, and manage subscriptions without ever leaving the chat window, which makes for a really smooth upselling experience.

The platform is explicitly designed to turn support into a way to make money. You can set up proactive chats that pop up on certain pages and use templates called "Macros" to suggest products. The catch is that the AI that provides genuine upselling intelligence is part of the "AI Agent," which costs extra and can make your monthly bill a bit of a moving target.

The Gorgias dashboard showing deep Shopify integration, a key feature for effective live chat upselling in e-commerce.

Pros & Cons

• Pros: Fantastic Shopify integration, a strong focus on revenue-generating features, and unlimited user seats on every plan.

• Cons: The pricing is based on billable tickets, which can add up quickly for busy stores. The most useful AI features tack on a per-resolution cost, which creates unpredictable bills.

Pricing

Gorgias pricing is based on billable tickets, with AI resolutions costing more.

• Starter: From $10/month for 50 tickets.

• Basic: From $50/month (billed annually) for 300 tickets.

• Pro: From $300/month (billed annually) for 2,000 tickets.

• Advanced: From $750/month (billed annually) for 5,000 tickets.

• AI Agent: An additional $0.90 to $1.00 per fully automated resolution.

3. Intercom

Intercom was one of the first to really nail proactive messaging, and it's still a major player with its slick Messenger and AI agent, "Fin." It's a complete, all-in-one platform built to engage customers through their entire journey.

For upselling, Intercom's strength is in its detailed workflow builder and targeting. You can build custom bots that qualify leads, suggest upgrades based on what a user is doing on your site, and pass them to a human agent at just the right moment. The main thing to watch out for is the pricing. You pay for each agent seat and for every resolution its AI, Fin, handles. That can get expensive, fast, especially as you grow.

A view of Intercom's workflow builder, which teams can use to create targeted live chat upselling campaigns.

Pros & Cons

• Pros: A very polished user interface, powerful proactive messaging tools, and can be used as a standalone AI agent on other helpdesks.

• Cons: The double-dip pricing (per seat + per resolution) is expensive and hard to predict. It's a full platform replacement, which can be a huge project to switch to.

Pricing

Intercom's pricing includes a per-seat cost plus a per-resolution fee for its AI.

• Essential: $29/seat/month (billed annually) + $0.99 per Fin resolution.

• Advanced: $85/seat/month (billed annually) + $0.99 per Fin resolution.

• Expert: $132/seat/month (billed annually) + $0.99 per Fin resolution.

• Standalone Fin AI: $0.99 per resolution with a 50-resolution monthly minimum if you use it with another helpdesk.

4. LiveChat

LiveChat is a dedicated chat tool that has grown to include more sales and support features. It’s pretty straightforward and does its job well, with a clear focus on helping agents sell more effectively in conversations.

Its coolest feature for upselling is "Product Cards." Agents can send these rich, interactive cards with product pictures, descriptions, and "add to cart" buttons right inside the chat. It's a much more engaging way to show off a product than just dropping a link. It also gives you solid reporting to see how many chats actually turn into a sale. While it does have an AI chatbot, it’s a separate product (ChatBot), so the AI isn't as tightly woven in as with other platforms.

A demonstration of LiveChat's Product Cards, an effective tool for visual live chat upselling.

Pros & Cons

• Pros: Great for sales-focused teams, Product Cards are a nice visual tool for upselling, and it has strong reporting for tracking sales.

• Cons: It's mostly just a chat tool, not a complete helpdesk. The AI chatbot is a separate product with its own subscription, which adds complexity and cost.

Pricing

LiveChat is priced per agent, with different tiers unlocking more features.

• Starter: $20/month per agent (billed annually).

• Team: $41/month per agent (billed annually).

• Business: $59/month per agent (billed annually).

• Enterprise: Custom pricing.

• ChatBot Add-on: Starts at an additional $52/month.

5. Tidio

Tidio is a go-to choice for small businesses and e-commerce stores, mostly because it has a pretty generous free plan to help you get started. It rolls live chat, chatbots, and email marketing into one simple package.

For upselling, Tidio uses its "Flows" feature, which is a visual builder for mapping out automated conversations. You can design flows that recommend products or offer discounts at key moments. Its AI agent, "Lyro," can answer customer questions by pulling from your knowledge base. The only snag is that the free and lower-priced plans have pretty tight limits on how many people your Flows can reach and how many AI conversations you can have, which can hold you back as you grow.

Pros & Cons

• Pros: A great free plan for small businesses, an easy-to-use visual flow builder, and it combines chat with basic marketing tools.

• Cons: The limits on AI and automation on the cheaper plans are strict, and it can get expensive as you scale up and need more of those features.

Pricing

Tidio's pricing is a mix of plans with different limits for human chats, AI chats, and proactive Flows.

• Free: Includes 50 live conversations and 100 proactive "Flows" visitors.

• Starter: $29/month for 100 live conversations.

• Communicator: $25/month per seat for unlimited conversations.

• Chatbots: Starts at $29/month for 2,000 triggers.

• Tidio+: Starts at $394/month for a more complete package.

Note: Tidio's website has been updated to reflect new plans (Communicator, Chatbots, Tidio+) instead of the Starter/Growth/Plus tiers previously listed.

6. Zendesk

You've probably heard of Zendesk; it’s one of the biggest names in the game. It's a massive, enterprise-level platform that handles everything from ticketing to knowledge bases. Its live chat and AI features are all part of this huge ecosystem.

Upselling in Zendesk usually happens through a mix of its Answer Bot and proactive triggers. You can set up bots to suggest help articles or pass a chat to an agent when a customer is looking at a key page. The biggest hurdle is that Zendesk is an all-or-nothing deal. You have to commit to their entire platform. And while it's powerful, its AI can feel less flexible than newer, AI-focused tools, and getting the advanced AI features often means upgrading to pricey plans or buying add-ons.

The Zendesk Agent Workspace, which provides a comprehensive environment for live chat upselling and support.

Pros & Cons

• Pros: A true all-in-one platform for large teams, powerful and can handle huge volumes, and has an extensive marketplace of integrations.

• Cons: It requires a full migration to their system, can be complicated and expensive to set up and manage, and the AI features on lower plans can be pretty basic.

Pricing

Zendesk offers tiered plans priced per agent.

• Suite Team: $55/agent/month (billed annually). Includes basic AI with limits.

• Suite Growth: $89/agent/month (billed annually).

• Suite Professional: $115/agent/month (billed annually).

• Advanced AI Add-on: Starts at an additional $50/agent/month.

7. Freshdesk

Freshdesk is another one of the big all-in-one helpdesk platforms and a major competitor to Zendesk. It's part of the wider Freshworks family and gives agents a single place to handle conversations from email, chat, and phone.

For upselling, Freshdesk leans on its "Freddy AI" to run its chatbots and assist agents. Freddy can suggest articles, answer common questions, and get chats to the right team. The platform is solid, but like Zendesk, it asks you to adopt their whole system. The AI features also come with extra costs, either as add-ons or through session-based pricing, which can make budgeting a bit tricky.

Freshdesk's Freddy AI Copilot assisting an agent with suggestions, a useful feature for live chat upselling.

Pros & Cons

• Pros: A unified platform for omnichannel support, a user-friendly interface for agents, and great for teams already using other Freshworks products.

• Cons: It’s a full platform migration, and the AI features often cost extra and can be based on a "per session" model.

Pricing

Freshdesk offers several tiers, with AI features often costing extra.

• Free: Up to 10 agents.

• Growth: $15/agent/month (billed annually).

• Pro: $49/agent/month (billed annually).

• Enterprise: $79/agent/month (billed annually).

• Freddy AI Copilot Add-on: $29/agent/month.

• Freddy AI Agent: Billed at $100 per 1,000 sessions after an initial free allotment.

How to choose the right tool for live chat upselling

Feeling a bit swamped by all the options? Don't worry. Picking the right tool really just comes down to answering a few simple questions:

• Do you actually like your current helpdesk? If you have a system like Zendesk or Freshdesk that your team knows and works well in, a tool like eesel AI that plugs right into it is your best bet. You get all the AI power without the migration nightmare.

• What does your budget really look like? Be careful with pricing that charges you per agent and per resolution. Models like Intercom's can get out of control in a hurry. A flat-rate tool gives you predictability, so you can focus on your customers instead of counting tickets.

• How much control do you need? If you want to get granular with your AI's tone of voice, control exactly when it messages someone, and test everything in a safe environment before launch, look for tools that offer deep customization and simulation.

Final thoughts on live chat upselling

Trying to turn your support team into a sales team is usually a recipe for unhappy employees and annoyed customers. But you can't just leave money on the table, either. The right way to do live chat upselling isn't about pushing products, it's about being proactively helpful. It’s about understanding a customer’s situation so well that you can offer them a better solution before they even think to ask.

While the giant platforms like Zendesk and Intercom have a lot to offer, they often come with big price tags, complicated setups, and the headache of moving your entire workflow. For teams that want to move quickly and add smart upselling to the way they already work, a flexible, self-serve tool is the way to go.

eesel AI lets you get started in minutes, learns from your team's unique voice, and gives you the control you need to roll out automation with confidence. You can add a powerful AI layer to the tools you already love, turning every single conversation into a chance to build trust and grow your business.